Could CHI Cubs Pivot From Kyle Tucker Pursuit to Tarik Skubal Trade Soon?

This week, a Chicago Cubs insider made the case for why the club should pursue a trade for Tarik Skubal this winter and let Kyle Tucker walk in MLB free agency.

The 2025 season was a big step forward for the Cubs. After a pair of 83-79 seasons, the franchise needed to finally prove they have evolved into a real threat to the NL Central’s top team, the Milwaukee Brewers. Without a doubt, Seiya Suzuki and Pete Crow-Armstrong played a big role in their 92-win campaign. However, it likely doesn’t happen without the addition of Kyle Tucker in the offseason.

Did the four-time All-Star disappoint in the second half? Sure, but what he was able to bring over the first few months is why The Athletic’s Patrick Mooney suggested on Tuesday, Chicago is probably satisfied with their trade for Tucker. Even though it’s likely they will lose him in free agency in the coming weeks.

The Cubs have the financial resources to match any offer the star outfielder gets this offseason. However, considering the likely price and the aforementioned second-half slump, it’s logical that Tucker is one-and-done in Chi-town. So what could the team do to fill that void and stay in title contention next season? Well, the obvious assumption would be to go get a big bat, but maybe not.

Should the Cubs pivot to an all-in trade for Tarik Skubal now?

“Trading for Tarik Skubal would be another way to look at the situation if the Cubs were hellbent on trying to win the 2026 World Series,” Mooney writes. “Coming off a 92-win season and five electric playoff games at Wrigley Field, the Cubs should have the requisite resources and sense of urgency to make a deal for one of the best pitchers on the planet.”

Skubal is expected to garner a contract worth over $400 million after the 2026 season. Mooney points out the Cubs only have a few players on the books in 2027. Meaning, they have more than enough free money to give the two-time Cy Young winner whatever deal he wants.

The Cubs insider also pointed out that Chicago had just one pitcher in the recent Baseball America ranking of their top 10 prospects. They don’t have impact arms on the way, so they will keep having to outsource to improve that position. So why not do it by going after the best in the game, who is just entering his prime?

“For a multibillion-dollar franchise, making Skubal the highest-paid pitcher in baseball history could be a smart investment,” Mooney wrote.

The other question is, do the Cubs have the prospect assets to get a trade done? The top prospect in their system, Owen Caissie, barely landed in the top 50 of MLB.com’s rankings of the best in all of baseball right now.

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